Sodium Carbonate → HCID 44124988, compound

Participants

Reaction Conditions

Reaction Steps

A sealable vial was charged with N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (81 mg, 196 μmol), N-(6-chloro-3-(pyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide-TFA salt (47.0 mg, 163 μmol), sodium carbonate (69 mg, 653 μmol) and dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium(II) (9.1 mg, 16 μmol). The vial was sealed with a septum cap and 1,4-dioxane (2 mL) and water (0.2 mL) were added under positive N2 flow. The mixture was sparged for 10 min with N2 and heated at 90° C. for 18 h. The solution was cooled to rt and concentrated for purification by MPLC (CombiFlash® Companion®, Teledyne Isco, Lincoln, Nebr.). The residue was taken up in minimal CH2Cl2/MeOH and absorbed onto a 25 g silica loading cartridge and passed through a Redi-Sep® pre-packed silica gel column (80 g) (Teledyne Isco, Lincoln, Nebr.) using a gradient of 1% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2 to afford the title compound, N-(6-(6-chloro-5-(4-fluorophenylsulfonamido)pyridin-3-yl)-3-(pyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (23 mg, 26% yield) as a yellow solid. LCMS (ESI positive ionization) m/z: 538.0 (M+1); 1H NMR (400 MHz, MeOH-d6) δ ppm 2.27 (s, 3H) 7.95-8.07 (m, 2H) 8.21 (dd, J=61.57, 9.54 Hz, 2H) 8.63-8.71 (m, 3H) 8.76-8.81 (m, 2H) 8.82-8.86 (m, 2H) 8.87-8.92 (m, 2H).

Provenance & Evidence